CN102060818B - Novel spirodiclofen compound and preparation method and application thereof - Google Patents
Novel spirodiclofen compound and preparation method and application thereof Download PDFInfo
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- CN102060818B CN102060818B CN2011100029881A CN201110002988A CN102060818B CN 102060818 B CN102060818 B CN 102060818B CN 2011100029881 A CN2011100029881 A CN 2011100029881A CN 201110002988 A CN201110002988 A CN 201110002988A CN 102060818 B CN102060818 B CN 102060818B
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- Prior art keywords
- compound
- spiral shell
- novel
- shell mite
- spirodiclofen
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- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
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- -1 spirodiclofen compound Chemical class 0.000 title claims abstract description 29
- 238000002360 preparation method Methods 0.000 title abstract description 9
- 239000005664 Spirodiclofen Substances 0.000 title abstract 6
- 150000001875 compounds Chemical class 0.000 claims abstract description 23
- 150000002148 esters Chemical class 0.000 claims abstract description 13
- 239000002253 acid Substances 0.000 claims abstract description 5
- 239000011230 binding agent Substances 0.000 claims abstract description 5
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical group CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 claims description 15
- 238000000034 method Methods 0.000 claims description 15
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 12
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 11
- 239000002904 solvent Substances 0.000 claims description 11
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 8
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 8
- 150000001335 aliphatic alkanes Chemical group 0.000 claims description 7
- 150000004945 aromatic hydrocarbons Chemical class 0.000 claims description 4
- 150000002170 ethers Chemical class 0.000 claims description 4
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 4
- 238000001953 recrystallisation Methods 0.000 claims description 4
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 claims description 2
- BZLVMXJERCGZMT-UHFFFAOYSA-N Methyl tert-butyl ether Chemical compound COC(C)(C)C BZLVMXJERCGZMT-UHFFFAOYSA-N 0.000 claims description 2
- 150000003138 primary alcohols Chemical class 0.000 claims description 2
- FZFAMSAMCHXGEF-UHFFFAOYSA-N chloro formate Chemical compound ClOC=O FZFAMSAMCHXGEF-UHFFFAOYSA-N 0.000 claims 1
- 238000000926 separation method Methods 0.000 claims 1
- 238000010189 synthetic method Methods 0.000 claims 1
- 230000002147 killing effect Effects 0.000 abstract description 5
- 241000238876 Acari Species 0.000 abstract 1
- 241000607479 Yersinia pestis Species 0.000 abstract 1
- 239000000010 aprotic solvent Substances 0.000 abstract 1
- 238000001308 synthesis method Methods 0.000 abstract 1
- 238000006243 chemical reaction Methods 0.000 description 22
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 18
- 238000003756 stirring Methods 0.000 description 15
- 102000002322 Egg Proteins Human genes 0.000 description 6
- 108010000912 Egg Proteins Proteins 0.000 description 6
- 230000000895 acaricidal effect Effects 0.000 description 6
- 239000003795 chemical substances by application Substances 0.000 description 6
- 210000004681 ovum Anatomy 0.000 description 6
- 238000012360 testing method Methods 0.000 description 6
- 239000013078 crystal Substances 0.000 description 5
- 238000001035 drying Methods 0.000 description 5
- 239000005457 ice water Substances 0.000 description 5
- 230000006698 induction Effects 0.000 description 5
- 230000000749 insecticidal effect Effects 0.000 description 5
- 239000010410 layer Substances 0.000 description 5
- 239000007788 liquid Substances 0.000 description 5
- 239000012044 organic layer Substances 0.000 description 5
- 239000012074 organic phase Substances 0.000 description 5
- 230000035484 reaction time Effects 0.000 description 5
- 229920006395 saturated elastomer Polymers 0.000 description 5
- 238000005406 washing Methods 0.000 description 5
- 230000000694 effects Effects 0.000 description 4
- 239000003814 drug Substances 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- 241000238631 Hexapoda Species 0.000 description 2
- 239000000642 acaricide Substances 0.000 description 2
- 230000004071 biological effect Effects 0.000 description 2
- 229940079593 drug Drugs 0.000 description 2
- 230000006872 improvement Effects 0.000 description 2
- 230000010534 mechanism of action Effects 0.000 description 2
- 239000000575 pesticide Substances 0.000 description 2
- 230000008569 process Effects 0.000 description 2
- BSKHPKMHTQYZBB-UHFFFAOYSA-N 2-methylpyridine Chemical compound CC1=CC=CC=N1 BSKHPKMHTQYZBB-UHFFFAOYSA-N 0.000 description 1
- KCCKTIKZOIPZTG-UHFFFAOYSA-N 3-methylbutyl carbonochloridate Chemical compound CC(C)CCOC(Cl)=O KCCKTIKZOIPZTG-UHFFFAOYSA-N 0.000 description 1
- 241001425390 Aphis fabae Species 0.000 description 1
- DTDSAWVUFPGDMX-UHFFFAOYSA-N CCC(C)(C)C(OC(C1(CCCCC1)OC1=O)=C1c(ccc(Cl)c1)c1Cl)=O Chemical compound CCC(C)(C)C(OC(C1(CCCCC1)OC1=O)=C1c(ccc(Cl)c1)c1Cl)=O DTDSAWVUFPGDMX-UHFFFAOYSA-N 0.000 description 1
- 235000007516 Chrysanthemum Nutrition 0.000 description 1
- 244000189548 Chrysanthemum x morifolium Species 0.000 description 1
- KIKARNYYJSEROI-UHFFFAOYSA-N OC(C1(CCCCC1)OC1=O)=C1c(c(Cl)c1)ccc1Cl Chemical compound OC(C1(CCCCC1)OC1=O)=C1c(c(Cl)c1)ccc1Cl KIKARNYYJSEROI-UHFFFAOYSA-N 0.000 description 1
- 150000001263 acyl chlorides Chemical class 0.000 description 1
- YSMHTFWPDRJCMN-UHFFFAOYSA-N butan-2-yl carbonochloridate Chemical compound CCC(C)OC(Cl)=O YSMHTFWPDRJCMN-UHFFFAOYSA-N 0.000 description 1
- NRDQFWXVTPZZAZ-UHFFFAOYSA-N butyl carbonochloridate Chemical compound CCCCOC(Cl)=O NRDQFWXVTPZZAZ-UHFFFAOYSA-N 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 229910052956 cinnabar Inorganic materials 0.000 description 1
- 239000000470 constituent Substances 0.000 description 1
- 230000002401 inhibitory effect Effects 0.000 description 1
- 150000002632 lipids Chemical class 0.000 description 1
- XMJHPCRAQCTCFT-UHFFFAOYSA-N methyl chloroformate Chemical compound COC(Cl)=O XMJHPCRAQCTCFT-UHFFFAOYSA-N 0.000 description 1
- 230000003129 miticidal effect Effects 0.000 description 1
- PEQJBOMPGWYIRO-UHFFFAOYSA-N n-ethyl-3,4-dimethoxyaniline Chemical class CCNC1=CC=C(OC)C(OC)=C1 PEQJBOMPGWYIRO-UHFFFAOYSA-N 0.000 description 1
- 238000005554 pickling Methods 0.000 description 1
- IVRIRQXJSNCSPQ-UHFFFAOYSA-N propan-2-yl carbonochloridate Chemical compound CC(C)OC(Cl)=O IVRIRQXJSNCSPQ-UHFFFAOYSA-N 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 235000014347 soups Nutrition 0.000 description 1
- 125000003944 tolyl group Chemical group 0.000 description 1
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- Agricultural Chemicals And Associated Chemicals (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
Description
Claims (5)
Priority Applications (1)
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CN2011100029881A CN102060818B (en) | 2011-01-07 | 2011-01-07 | Novel spirodiclofen compound and preparation method and application thereof |
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CN2011100029881A CN102060818B (en) | 2011-01-07 | 2011-01-07 | Novel spirodiclofen compound and preparation method and application thereof |
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CN102060818A CN102060818A (en) | 2011-05-18 |
CN102060818B true CN102060818B (en) | 2012-02-01 |
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CN2011100029881A Active CN102060818B (en) | 2011-01-07 | 2011-01-07 | Novel spirodiclofen compound and preparation method and application thereof |
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2011
- 2011-01-07 CN CN2011100029881A patent/CN102060818B/en active Active
Cited By (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN103355328A (en) * | 2013-08-05 | 2013-10-23 | 杭州宇龙化工有限公司 | Mite-killing composition containing C20H22Cl2O5 and etoxazole |
CN103355328B (en) * | 2013-08-05 | 2015-07-22 | 杭州宇龙化工有限公司 | Mite-killing composition containing C20H22Cl2O5 and etoxazole |
CN108610315A (en) * | 2016-12-09 | 2018-10-02 | 浙江省化工研究院有限公司 | A kind of tetronic acid analog derivative, preparation method and application |
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Inventor after: Xu Liangzhong Inventor after: Wu Hualong Inventor after: Yin Ruifeng Inventor after: Feng Xianguo Inventor before: Xu Liangzhong Inventor before: Yin Ruifeng Inventor before: Feng Xianguo |
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